Permanent creasing of wool-containing fabrics



United States Patent Oflice 3,516,782 Patented June 23, 1970 US. Cl. 8127.6 10 Claims ABSTRACT OF THE DISCLOSURE A process for imparting permanent press properties to wool-containing fabrics comprising the steps of treating a shrinkproofed wool-containing fabric with an aqueous solution of either a sulfonium or ammonium compound in the presence of an alkaline catalyst; shaping the treated fabric in any desired manner and then setting the shape by heat-pressing the fabric.

This invention relates to a method for imparting to wool-containing fabrics durable creases, folds, pleats or other such structural arrangements as may be selected by the operator.

It is, of course, well known that wool garments are provided with some sort of fabric arrangement, for example, pleats, creases, etc. Such deformations are conventionally produced by ironing the garment while constrained in the desired pattern. With the advent of washable wool fabrics, the creases, pleats, etc., are required to be resistant to washing so as to avoid the necessity for restoring the desired shape by ironing.

One object of our persent invention is to provide for washable wool or washable wool-containing garments which are unrestricted as to style, size, design and shape, and which are ready to wear after repeated washings without pressing;

Another object of our invention is to provide improved washable wool-containing garments and an improved process of manufacture thereof which affords the utilization of chemically treated fabrics that have been retained on the shelf for an additional period without cutting for garment making;

Yet another object of the present invention is to provide improved garments and an improved process of the indicated nature wherein chemicals used for treating the wool garment fabrics are retained in an uncured condition on the fabric for an appreciable period of time without decomposition;

Other objects and many of the attendant advantages of this invention will be readily appreciated as the same becomes better understood by reference to the following detail description.

Briefly, this invention relates to a process for imparting crease retention capability to wool fabrics comprising the steps of treating in the presence of an alkaline catalyst a shrinkproofed wool fabric with an aqueous solution of a compound having the following structure:

RI 12 R" and R is a divalent hydrocarbon radical having from -1 to 18 carbon atoms and being selected from the group consisting of alkylene, alkenylene, phenylene, substituted phenylene, cycloalkylene and combinations thereof such as alkylcycloalkylene, alkarylene, cycloalkylalkylene, cycloalkylarylene, aralkylene, arylcyqloal kylene, cycloalkylaralkylene, and the like;

X is an anion;

Q is a moiety selected from the group consisting of G and Y, and

Y is any substituent having both the potential of forming an anion and of forming a covalent bond with a --CH group such as Cl, Br and I;

R, R" and R' are either hydrocarbon radicals or substituted hydrocarbon radicals having from 1 to 18 carbon atoms and being selected from the group consisting of alkyl, hydroxy-alkyl, alkoxy-alkyl, cycloalkyl, aryl, substituted aryl wherein the substituents are radicals selected from the group consisting of --SO H, Cl, N0 and COOH and R, R", R' combined can form a heterocyclic ring of which the N or S atom is also a part; shaping the treated fabric and reacting in situ the said compound with the W001 fabrics whereby the shaped fabric is press-free and retains any imparted crease after repeated washings thereof.

Under the prior art many processes have been developed for treating cotton fabrics so as to render them creaseproof when subjected to washing conditions. As representative of this type of prior art, Pat. Nos. 2,974,432 and 3,268,915 issued to William K. Warnock et a1., describe a method for impregnating a cotton fabric with a crease-resistant agent and then manufacturing the fabric into a garment before the agent is caused to react and impart the desired crease configuration into the cotton fabric. The prior art processes are not concerned with the problem of imparting crease retention capabilities to washable woolen and worsted fabrics. A German chemist by the name of Rath describes, in an article entitled Der Chemismus der Oniumverbindungen und ihre Bedeutung fiir die Textilchernie und Textilvere'dlung II Melliand Textilberichte 3 8 (1957) pp. 66=1-662, the treatment of reduced wool with water-soluble cleava ble bifunctional onium compounds to decrease the alkali solubility of the wool.

The ipossibility of reacting wool with the onium compounds without prior reduction to obtain permanent press effects was not recognized. Moreover, Rath did not appreciate that shrinkproofed W001 fabric would still be receptive to being treated with an onium compound, and the possibility of employing the reaction with onium compounds to impart crease retention was not implied or suggested in Raths work.

We have unexpectedly discovered that without prior reduction, shrinkproofed wool fabrics can be treated with an onium compound in the presence of an alkaline catalyst whereby the fabric can be shaped into a garment and the onium compound reacted to impart a permanent configuration to the garment.

It is to be understood that although cleavable onium compounds are preferred in the practice of this invention, noncleavable onium compounds were found to also impart good crease retention to the wool fabrics treated according to the process of this invention.

By the term cleavable onium compounds we mean to include those compounds described hereinabove wherein R contains unsaturation and are cleaved under milder conditions for use in our process.

It is essential that the starting material for the process be a shrinkproof fabric because any permanent shape or creases would obviously be both obscured and rendered useless by felting and dimensional changes during washing. As examples of shrinkproofing processes, U.S. Pat. Nos. 3,165,375 and 3,115,383 issued to Giuliana C. Tesoro described methods for shrinkproofing woolen and worsted fabrics useful in our process. It is therefore to be understood that the step of shrinkproofing the wool fabrics does not form a part of the inventive concept disclosed herein.

In the practice of our invention, each selected fabric from which garments are to be made is unwound from a roll thereof and passed through a conventional dipping or padding machine to be thoroughly treated with an aqueous solution of a watersolu'ble onium compound as set forth hereinabove. Preferably, the fabrics are dipped in the aqueous solution of the onium compound in order to insure approximately 85 to 100% pickup of the solution by the fabric whereby the fabric contains 1 to 10% by weight of the onium compound, preferably 4 to 8%, and although water is preferred as the most convenient and economical solvent, it is to be understood that any volatile inert solvent, for example, methanol, ethanol, dioxane, etc., can be employed as the carrier for the onium compound.

'It is also within the scope of this invention that other means of applying the onium compound to the fabric can be employed such as brushing, spraying, roller coating, etc.

When the onium compound is applied in aqueous solutions in the form of its iodide or bromide salt, the concentration thereof is usually from about 4 to about 10% by weight in a solution at 25 C. Usually it is preferred that the total amount of onium compound applied to the fabric be not over 10% based on the weight of the fabric so as to avoid changing the hand of the textile.

The fabric treated with the onium compound is passed through rollers for removing excess solution but the rollers and the concentration of the solution are so controlled that at least 2% by weight of the onium compound is retained in the fabric.

Thereafter, the treated fabric is dried. The drying temperature to which the fabric is subjected is maintained between approximately 120 to 250 F. and preferably from 150 to 200 F.

The drying of the fabric is controlled so that the onium compound does not react with the wool.

The onium solution can also contain a conventional Wetting agent to assist in penetration of the solution into the structure of the woolen textile.

A satisfactory but not exhaustive list of these wetting agents appears among other places in Soap and Chemical Specialties, vol. 31, No. 7, page 61; No. 8, pages 48-61; No. 9, pages 52-67, and N0. 10, pages 38-67 (1955).

I Only a small amount of wetting agent is needed, about 0.05 to 0.5% by weight in solution.

The solution can also contain a hygroscopic additive such as urea, ethylene glycol, glycerol, or the like, so as to give an add-on from 2 to 15, preferably 5 to by weight based on the weight of the fabric. These additives help retain moisture in the fabric and avoid the need for spraying the treated fabric prior to heat-pressing.

Examples of suitable alkaline agents useful in our process are alkali metal hydroxides, bicarbonates, carbonates, tetra-borates, phosphates, pyrophosphates, alkoxides, or other water-soluble salts which exhibit an alkaline buffering capacity, alkali carbonates being preferred. The amount of alkaline agent is regulated so that the solution has a pH of about 8 to 11.5, preferably about 9 to 10.

Whenever it is desired to manufacture garments in any style, size, type or design from any fabric processed as hereinabove set forth, the requisite amount of yardage of the fabric is removed from storage and delivered to a garment cutting room. Fabric is cut, sewn and finished in the garment cutting room and is transferred to a space containing suitable pressing equipment for imparting creases in the completed garments at locations therein consistent with the style and design of each garment.

The creases are permanently set by steampressing at a temperature ranging from 200 to 400 F. and preferably from 200 to 250 F., said temperature being sufiicient to effectuate reaction of the onium compound With the wool-containing fabric. The residence time of the garment within the steam presser ranges from 0.25 minute up to 30 minutes, and preferably from 1 to 15 minutes.

The permanent setting step is usually conducted in the presence of moisture; however, the moistening of the fabrics prior to steam-pressing can be avoided by adding hydroscopic agents to the sensitizing solution as explained hereinabove, or by exposing the samples to superactivated steam for a longer period.

It is also within the scope of this invention to enhance the shape retentive characteristics of the set wool fabric by subjecting it to a curing step. It is to be appreciated that different temperatures are required to cure the treated fabric in different garments, such variations in setting temperatures being dependent in part upon the nature and texture of the fabric of which the garment is made and in which the onium compound is contained. The range of temperatures in the curing oven is from 200 to 350 F., preferably 250 to 300 F. and the curing time ranges from 2 to 15 minutes, preferably 5 to 10.

In another embodiment of this invention the solution of onium compound can also contain a reducing agent which does not react with the onium compound. The concentration of the reducing agent is from 0.10 to 5% by weight of the solution. Suitable reducing agents are alkali borohydrides and formaldehyde sulfoxilate.

It is to be understood that at this point the solution of onium compound can be altered to some extent without departing from the spirit of our discovery as the essence of our concept hereinafter claimed is that the onium solution remains unreacted with the wool-containing fabric until after the completion of the pressing step.

The process of the invention may be applied to woolcontaining textiles in the form of threads, fibers, yarns, slivers, rovings, woven fabrics, knitted fabrics, felts or garments made of woven or knitted fabrics. The textiles may be White or dyed goods. Typical applications of the invention are: To provide garments with pleats, creases, or other arrangements customary in tailoring; to provide sheets of fabric with preformed pleats so that the product can be used for the fabrication of skirts, draperies, etc., to produce crimp, twist, or other configurations in yarns, threads, and the like.

The invention is further demonstrated by the following illustrative examples:

EXAMPLE I In order to compare the creasing efficiency of various onium compounds, separate samples of an allwool, reddyed tropical worsted fabric stabilized according to the teaching of U.S. Pat. 3,279,882 were padded with aqueous solutions of the various onium compounds in the presence of potassium carbonate. A 0.1% by weight of a nonionic wetting agent (isooctylphenylether of polyethylene glycol) was incoporated into the solutions. The presensitized samples were dried to normal moisture content, creased, and steam-pressed for one minute at 220 F. Some of the samples were then sprayed with water before pressing as indicated in the table set forth hereinbelow.

Crease Itet, 5 Wash/Wear, 5

133311111; Pertcyergg Launderings l Launderings 2 33333 332333 33353 Spray- Tumble Onium Treating Compound Fabric Fabric Fabric ing Damp 3 Dry Damp 3 Dry (1,4-phenylenedimethylene) bis [dimeth ylphenylammonium bro- 7. 8 3. 9 4. 5 3. 3 4. 3 4. 3

(1,4-phenylenedimethylene) bis [bis(2-hydroxyethyl) sulfonium bromide]. 11. 7 3. 5 3. 5 4. 3

2-butenylenebis[dimethylphenylammonium bromide] 10. 5. 0 4. 0 3.0 3. 8 3.

tetramethy1enebis[dimethylphenylammonium bromide] 8. 6 4. 3 4. 0 2. 5 3. 0 2. 8

(1,4-phenylenedimethylene) bis[trimethylammonium chloride]. 6. 2 4. 0 4. 0 2. 5 2. 5 4. 3

(1,4-phenylenedirnethy1ene)bis[pyridiniu m chloride] 5. 8 3. 8 3. 0 1. 5 2. 0 4. 5

(1,4-phenylenedimethylene)bis[pyridi.minm bromide] 9. 6 4. 8 3. 0 2. 0 8. 0 4. 3

C ontrol 1 AAT)C C88C1964T (Test II C): 5=Negligible or no change; 4=Slight change; 3=Noticeable change; 2=Considerable change; 1=N one (completely removed 2 AATCC88A-1964T (Test II CO-Wash and wear characteristics were rated on the following scale: 5=Negligible or no change; 4=Slight change; 3=Noticeable change; 2= Considerable change; l=N one (completely removed).

3 Damp=Fabric laundered according to the AATCC Test Methods for wash and wear and crease retention except the fabric is removed from the tumble dryer in a slightly damp state and hung up for complete drying before ratlng.

It is observed that the crease retention of the samples reducing agents. The operating procedures were carried which were sprayed prior to steam-pressing was satisout as in Example I. The results are shown in the folfactory after line drying and also after tumble drying lowing table:

Samples exposed to 15 minutes steam Samples steam pressed for 1 minute ing after 1 minute of steam pressing Crease reten., Wash/wear, Crease reten., Wash/wear, b Percerlrlti; 5 launderings 5 launderings 5 laundcrings 5 launderings y weig Percent Percent of For- Tumble Tumble Tumble Tumble by weight 1 by weight maldehyde- Llnc dry Lme dry Line dry Line dry Run No. of K2003 of NaBH sulioxilate dry damp dry damp y damp dry damp 1 All weights are based on the weight of the sensitizingsolution. No'rrL-It is apparent from the experiments described in this Example that comparable crease retention values were obtained in the presence and in the absence of reducing agents and that one mlnute steam pressing was sufliclent. especially when they were removed from the tumble EXAMPLE III dryerinadamp State A series of experiments was carried out to study EXAMPLE H the effect of hygroscopic agents on the crease retentive The following series of experiments were carried out capabilities of a sensitizing solution comprising (1, in order to compare the efficiencies of reducing agents 4 phenylenedimethylene)bis[dimethylphenylarnmonium present in the sensitizing onium solution. In these exbromide] and potassium carbonate. The hygroscopic periments, samples of the wool fabric used in Example I agents were selected from the groups consisting of urea, were treated with a solution containing (1,4-phenyleneethylene glycol, and glycerol. Both the wool fabric and dimethylene)bis[dimethylphenylammonium bromide] and the operating conditions were the same as in Example potassium carbonate with and without the addition of I. The results are as follows:

Percent of Percent of Amount of Crease Reten., Wash/Wear, Shrinkage Onium Potassium Hygroscopic 5 Launderings 5 Launderings (percent), 5 Reagent Carbonate Additive Launderings Based on Based On Based on Tumble Dry Tumble Dry Weight of Weight of Weight of Spray- Fabric Fabric Fabric ing Damp Dry Damp Dry Warp Filling 91 45 45 2.5 3.5 4.0 4.0 5.0 9 3 4 6 Urea, 5%- 4.0 2.5 3.8 4.0 3. 5 5.0 8.2 4.1 Urea,5% 4.0 3.0 3.0 3.5 4.5 5.0 8.2 4.1 Ethylene glycol, 10%.. 3.8 2.5 3.0 4.3 3.0 4.0 7.7 3.8 Ethylene glycol, 10%-- 4 5 2.5 4.0 3.5 5.0 6.0 7.6 3.8 Glycerol, 10% 3 5 2.5 3.5 4.5 3.5 4.0 7.3 3.6 Glycerol, 10% 4 0 3.0 3.8 4.0 5.0 6.0

l (1,4-phenylenedimethylene)bisldimethylphenylammonium bromide].

2 Run 1 is a control run.

Nora-As evidenced by the above data, addition of a hygroscopic agent to the sensitizing solution eliminates the need for spraying prior to the steam pressing operation.

EXAMPLE IV Another series of experiments was conducted on the fabric of Example I to study the storage stability of sensitized onium compounds used in Examples II and It is apparent from the experiments described in the example that the crease retention of the wool fabrics were favorably affected either by moistening of the fabric prior to steam-pressing, by the addition of hygroscopic agents to the sensitizing solution, or by a post curing after steam- III. The presence or absence of a hygroscopic agent is pressing. Furthermore, the setting process does not affect noted in the following table:

tear and tensile strength and dimensional stability of the Crease Retention-3 Launderings Wash/Wear-3 Launderings Days Elapsed Between sensitizing and Pressing Percent cent TD TD TD TD TD TD Run Reagent K203 p y- OWF OWF Additive ing Damp Dry Damp Dry Damp Dry Damp Dry Damp Dry Damp Dry 11.4 6 8.3 4.4 Glycerol, 10%..- 4.0 2. 8 3. 5 2. 0 2. 5 2.0 3.0 4.8 2. 5 4.3 4.0 3.0 7 8.3 4.3 Glycerol, 10% 4. 5 2. 5 4. 3 2. 5 4.3 3.0 3.0 4.3 3.0 3.0 2.5 3. 5

1 Run 1 is a control run.

Norm-As evidenced by the data, the sensitized onium compound possessed excellent storage stability The moistening of the fabric can be avoided by adding a hygroscopic agent to the sensitizing solution.

EXAMPLE V In order to demonstrate the effect of employing a hygroscopic agent and of employing a subsequent heatcuring on the performance and physical properties of shrinkproofed wool fabrics; however, there is some increase in the stiffness of the treated wool fabrics.

Obviously, many modifications and variations of the present invention are possible in the light of the above the creased fabrics, the following series of experiments f 1S g g fi q g that wlghin the was performed. In these experiments, 100% woolen and 9 0 e.appen e c e mven may e prac' worsted fabric samples were shrinkproofed and were need j than.as speclficany descnbed heremabove' then treated with (1,4-phenylenedimethylene)bis[dimethiz 1s clalmgd 1 ylphenylammonium bromide] in the presence of K CO process. i lmpaftmg 3 retentlon to washas set forth in Example L The sensitized Samples were able woo1-contaimn.g fabrics comprising the stepsof treatdried to remove moisture content and then creased and mg m the p p i a1} alkalme .catailyst afimmkpropf stearmpressed for one minute Th6 results are set forth wool-containing fabric with a solution 1n an mert volatile hereinb 610w, solvent of an onium compound having the following 40 structure:

P t o C gr iit i r n Percent Percent (fi l i i ir Q CHE-R H2 G 3: fi fi 63 X i}? wherein G is a moiety selected from the group consisting o 1 100% woolen. 7.8 4.0 f g "i1 3'3 4'3 l g 1 R"X and s x- 0-... 6 do 8.6 4. 4 R R s-z r: i 9111111166 2, x'ifs't'e'rij 5'. 7 3:0 R is a divalent hydrocarbon radical having from 1 to 18 3:8 1 T carbon atoms and being selected from the group con- 5.7 3.0 sisting of alkylene, alkenylene, phenylene, cycloalkyg i I lene, alkylcycloalkylene, alkarylene, cycloalkylalkyg-i l i lene, cycloalkylarylene, aralkylene, arylcycloakylene,

These samples were then subjected to the following and cycloalkylaralkylene; X is an anion; Q is a moiety selected from the group consisting of G Crease Retention, Wash/Wear,

3 Launderings 3 Launderings Percent Shrinkage,

Tumble Dry Tumble Dry 3 Launderings Tensile Tear Flex Run Strength, Strength, Abrasion, Stiffness, N0. Damp Dry Damp Dry Warp Filling lbs. arp lbs. Warp Cycles/Warp Warp 1. 5 1. 0 3. 0 4. 3 4. 0 4. 0 20 2. 7 355 240 4. 3 2. 5 3. 5 3. 8 4. 0 5.0 18 2. 3 255 178 3. 0 2. 0 3. 0 4. 0 3. 5 4. 0 20 2. 5 415 222 3. 5 2. 5 3. 0 3. 5 5. 0 5. 0 19 2. 5 315 204 2. 0 2. 0 2. 0 4. 5 3. 5 4. 0 17 2. 6 235 304 4. 0 2. 5 3. 0 4. 0 4. 0 5. 0 19 2. 9 475 200 3. 5 2. 0 3. 5 4. 0 3. 5 4. 0 18 2. 5 205 308 4. 3 2. 5 3. 0 3. 0 5. 0 5. 0 19 2. 7 350 212 2. 5 4. 0 5. 5 5. 5 18 2. 9 575 164 1. 0 1.0 1. 0 3. 0 3. 0 l. 0 44 3. 7 650 291 l. 5 1.0 2. 0 3. 0 2. 5 1. 0 47 4. 3 775 225 1. 0 1. 0 1. 5 2. 8 3. 0 1. 0 47 4. 0 665 238 2. 0 1. 5 1. 0 3. 0 3. 0 1. 0 44 4. 3 1,050 191 1. 0 1. 0 1. 5 3. 0 3. 0 1. 0 44 4. 2 945 308 4.3 1. 5 1.5 3.0 3.0 2.0 42 4.3 775 213 2. 0 1. 5 1.0 3. 5 3. 0 None 43 3. 9 750 305 4. 5 2. 0 3. 0 3. 5 3. 5 2. 0 41 4. 0 l, 025 173 1. 5 3. 0 3. 0 +1. 0 43 4. 6 1, 425 202 1 Ravel Strip Method OOCT191(b) Method 5104.2.

2 ASTM D-142463.

3 Stoll Flex Ablader AS'IM D-1175-61T 11). head, 2 lbs. toggle); 4 ASTM D138855T Cantilever Method.

and Y, and Y is a substiutent selected from the group consisting of Cl, Br and I;

R', R" and R' are either hydrocarbon radicals or substituted hydrocarbon radicals having from 1 to 18 carbon atoms and being selected from the group consisting of alkyl, hydroXy-alkyl, alkoxy-alkyl, cycloalkyl, aryl, substituted aryl wherein the substituents are radicals selected from the group consisting of SO H, C1, N and COOH and R, R", R' can form a heterocyclic ring of which an N or S atom is also a part,

the amount of onium compound added to the fabric by said treatment being equal to about 2 to by weight of said fabric; drying the treated wool-containing fabric employing conditions under which the onium compound does not react with the Wool; shaping the treated fabric into a configuration which includes at least one crease and permanently setting the fabric in said configuration by reacting in situ the said onium compound with the fabric, said reaction being carried out by heating at a temperature of 200 to 400 F. in the presence of steam.

2. A process according to claim 1 further including the step of incorporating a reducing agent into the treating solution.

3. A process according to claim 1 further characterized in that the solution is an aqueous solution of said compound.

4. A proces according to Claim 1 wherein prior to the reaction step water is applied to the fabric and said fabric is in a moist condition when the reaction step is begun.

5. A process according to claim 1 including the step of incorporating a hygroscopic agent in the treating solution.

6. A process according to claim 2 further characterized in that the reducing agent is selected from the group 10 consisting of alkali borohydrides and formaldehyde sulfoxilate.

7. A process according to claim 5 further characterized in that the hygroscopic agents are selected from the group consisting of ethylene glycol urea, and glycerol.

8. A process according to claim 1 further including the step of heat-curing the treated fabric subsequent to the reaction step at temperatures ranging from 200 to 350 F.

9. A proces according to claim 1 further characterized in that the onium compound is (1,4-phenylenedimethylene bis (dimethylphenylammonium bromide) 10. A process according to claiml wherein said onium compound is selected from the group consisting of (1,4- phenylene dimethylene) bis (dimethylphenylammonium bromide); (1,4-phenylene-dimethylene) bis [bis(2-hydroxyethyl) sulfonium bromide]; 2. butenylene bis (dimethylammonium bromide); tetramethylene bis (dimethylphenyl-ammonium bromide); (1,4-phenylenedimethylene) bis (trimethylammonium chloride); (1,4 phenylene-dimethylene) bis (pyridinium chloride) and (1,4-phenylenedimethylene) bis (pyridinium bromide).

References Cited UNITED STATES PATENTS 3,216,781 11/1965 Pardo et al 8l27.6

FOREIGN PATENTS 1,020,954 12/1957 Germany.

GEORGE F. LESMES, Primary Examiner J. R. MILLER, Assistant Examiner U.S. Cl. X.R. 

